HCID 86722768, compound → HCID 28181729, compound

HRID 587787Notes

Reaction equation

HRID 587787 reaction equation
[CH3:1][CH:2]([CH3:23])[C@@H:3]([NH:12]C(=O)OCC1C=CC=CC=1)[C:4](=[O:11])[NH:5][CH2:6][C:7]([F:10])([F:9])[F:8].[H][H]>CCOC(C)=O.CCO.[Pd]>[NH2:12][C@H:3]([CH:2]([CH3:23])[CH3:1])[C:4]([NH:5][CH2:6][C:7]([F:8])([F:9])[F:10])=[O:11]

Participants

6

Reactant 2

HCID 86722768HCID 86722768, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 28181729HCID 28181729, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A Parr shaker flask charged with (R)-benzyl (3-methyl-1-oxo-1-((2,2,2-trifluoroethyl)amino)-butan-2-yl)carbamate (4.95 g, 14.9 mmol) in 100 mL of EtOAc and 25 mL of EtOH was treated with 175 mg of 10% Pd/C. The mixture was placed under 40 psi of hydrogen and shaken for 6 h. An additional 65 mg of 10% Pd/C was added to the reaction mixture which was then placed under 40 psi of hydrogen and shaken for 3.5 h. The reaction solution was then filtered through a pad of celite, concentrated in vacuo and purified by sublimation (75 to 85° C., 200-230 millibar) to afford the title compound as a white solid (1.92 g, 65%): mp 43-47° C.; 1H NMR (400 MHz, CDCl3) δ 8.04-7.74 (m, 1H), 3.92 (ddd, J=16.0, 9.3, 6.8 Hz, 1H), 3.84-3.60 (m, 1H), 3.23 (d, J=3.8 Hz, 1H), 2.23 (ddd, J=10.7, 7.0, 3.5 Hz, 1H), 0.92 (d, J=7.0 Hz, 3H), 0.75 (d, J=6.9 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −72.70.

Workup

  1. stirringshaken for 3.5 h
  2. filtrationThe reaction solution was then filtered through a pad of celite
  3. concentrationconcentrated in vacuo
  4. custompurified by sublimation (75 to 85° C., 200-230 millibar)

Sources & evidence

ORD record
ord-61d58e9516924c3283f2ac82bf4e5c67
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

Loading…